Vacation Rental Specialist (Streamline PMS)

About Us We’re Extenteam, a dynamic company revolutionizing the short term vacation rental industry. Our proven business model has generated consistent revenue, and we are now expanding from a professional services model to a scalable tech-based subscription-first model. As a scaling stage startup, we aim to grow our Monthly Recurring Revenue (MRR) to double our revenue by January 2026 by providing an AI assisted SaaS platform that works for all short term rental businesses regardless of their size. Extenteam is on a mission to streamline and support vacation rental businesses by providing top-notch solutions, including guest communication and property management support. We generate revenue through two primary streams: Dedicated Team Members: Providing trained overseas talent with a recurring premium model, replacing one-time recruitment fees. Tailwind - SaaS Platform: A guest communication Software blended with our shared services team, supporting smaller operators typically with less than 50 units - helping Extenteam increase profitability while growing our product market fit and expanding TAM and service levels. Extenteam is a small but mighty team of 50 consisting of Sales, Partner Success, Marketing, HR & Recruiting, Engineering, Product and Admin (IT, Data etc). We are spread out across the world but we have hubs in Miami, LA, Medellin, and actively expanding into Europe. Our 50 people core team is supported by 400+ DTMs (dedicated team members) that are servicing our customers. Our Values: Commitment to Excellence: Continuously raising the bar and setting new standards in guest communications and service delivery. Exceptional Collaboration: Thriving in a fast-paced, high-performance environment built on clear communication and teamwork. Unified Purpose: Aligning behind a shared mission to drive success with an intense focus. One shared consciousness. Data-Driven Decision-Making: Prioritizing data and results over emotions when making objective, professional decisions. Emphasis on Details: Details matter at every level. Leaders are expected to have a deep understanding of the specifics and adopt a hands-on management style. Our Leadership Philosophy Our company embraces a management style inspired by the ideals of "founder mode," as championed by Airbnb’s Brian Chesky. This means a hands-on, visionary approach to leadership, with a relentless focus on innovation, product excellence, and customer-centric decision-making. We encourage proactive problem-solving, direct involvement in key initiatives, and a collaborative, high-performance culture. To learn more about the "founder mode" philosophy and how it shapes our operations, you can explore this link . Understanding this mindset will provide valuable context for how we operate and what we value in our team members. What This Role Is About: We are looking for a Remote Vacation Rental Specialist for a Property Management Company Client of ours. This position is pivotal in providing outstanding customer service, managing reservations efficiently, and supporting back-office operations. The ideal candidate will excel in working independently, communicating effectively in a virtual setting, and ensuring a seamless experience for guests and internal teams. Your Main Responsibilities: Guest Services: Serve as the primary contact for guests, delivering exceptional customer service. Respond to in-house guest emails, chats, and texts through professional and friendly written communication to assist with issues such as lockbox, wifi troubleshooting, directions to homes, etc. Answer in-house guest calls and assist with issues such as lockbox, wifi troubleshooting, directions to homes, etc. Make outbound calls to incoming guests before arrival to ensure their needs are met. Respond to complaints or upset guests while maintaining professionalism and expressing empathy. When needed, escalate to the appropriate department or manager. Enter work orders for maintenance as issues are called or emailed in from guests. Guest Reservation Management: Communicate with potential guests in professional and friendly written communication via email, chat, and text. Respond to emails with reservation information, confirmations, and additional details. Collaborate with guests to understand their needs, recommend suitable properties, and answer questions regarding rooms, facilities, and rates. Become familiar with the area, company properties, and local attractions to be able to answer guest inquiries and questions. Advise customers regarding ongoing promotions or available upgrades that may enhance their experience. Respond to written guest inquiries via Airbnb, Vrbo, or other OTA messaging platforms. Answer phones and manage the end-to-end reservation process, including converting guest inquiries to bookings and assisting guests in altering or canceling reservations. Check voicemail and make outbound calls to follow up with potential guest inquiries and convert inquiries to bookings. Manage sales leads using any CRM / lead-tracking software. Process guest payments. Guest Feedback Management: Check and respond to guest reviews. Collect and analyze virtual guest feedback to identify areas for improvement and enhance overall guest satisfaction. Back Office Support: Assist property owners with questions. Process daily reservation reports. Contribute to back-office operations, handling tasks such as data entry, record-keeping, and documentation. Coordinate with internal teams, including housekeeping and maintenance, to support the efficient operation of vacation rental properties. Data entry for onboarding of properties into PMS, AirBnB or VRBO listings. Update listings in OTA systems, including property photos, rates, and descriptions. What We’re Looking For: Excellent written and verbal English skills for phone, text, and email communication. Previous experience in guest services, reservations, or a related field. Strong organizational and multitasking abilities. Ability to work independently in a remote work environment. Attention to detail and commitment to providing exceptional service. Ability to show empathy, exhibit patience, and have a customer-centric mindset Possess critical thinking and problem-solving skills. Ability to learn new software quickly and efficiently. Willingness to ask questions when unclear about a task or process. Nice to Haves: Vacation rental industry experience, working with VRBO, AirBnB, etc. PMS experience in the rental and hotel industry. Technical Requirements: Internet speed minimum 30mbps: Needs to be Wired (Buy a dongle if no LAN port) i5 11th Gen or higher Windows 11 / MacOS Catalina or higher Minimum of 8 GB RAM Private and quiet dedicated home office area (no roosters, dogs, children's noises in the background) Back-ups in case of power or internet provider interruptions Good headset and webcam (preferably noise-canceling headset) Why You’ll Love Working with Us: Competitive Salary — We offer a competitive salary that reflects the candidate’s experience, skills, and responsibilities. Remote Work — This role is 100% remote, allowing flexibility and eliminating daily commute. Paid Time Off — Standard leave entitlements (vacation, sick leave, vacation leave) for rest and well-being. HMO Coverage — Company-provided HMO plan, offering access to medical services via accredited hospitals and clinics under a Health Maintenance Organization. This helps ensure employees have access to routine checkups, consultations, and coverage for medical care.